He Deserves A Shot (At Being Happy)
by ChronicOlicity
Summary: Short version: an AU where Tommy Merlyn didn't die, and is around for the events preceding season 2 of Arrow (longer summary in body). Olicity-oriented fic, with some fun Tommy/Team Arrow interactions, Oliver having his head up his ass, and a dose of angst from a major death in the Undertaking.


**Summary:**  
 **Tommy Merlyn has spent most of his life being an expensive disappointment to his family, but now he's a part-owner of a semi-successful nightclub in the worst area of town (it's seriously looking up) alongside his best friend, who — after five years on a deserted island — decided to come back to be a freaking vigilante. It's a long story, one that's longer than Tommy wants to remember, but it took the Glades collapsing and the death of one of their best friends to get him officially done with being a troublemaker. Nothing interesting. Just running a nightclub, and trying not to get into any trouble.**

 **Oliver's been gone god knows where for most of the summer, which means he's stuck being the big brother to the guy's snarky little sister, whose boyfriend "Ron" seems completely set on getting himself killed. An afternoon of test-driving Verdant's new cocktails gets interesting when Felicity Smoak and John Diggle show up asking (more) questions about where to find Oliver, Tommy has to decide whether he wants to keep his new rule.**

* * *

 **Author's notes: Hey! So I know I've been dead silent on for a while, but it's mostly because of convenience. I've been posting new stuff to my account on AO3 (same name ChronicOlicity). Feel free to check out what I've been up to since then, or gimme a poke on Tumblr (again, same name).**

 **Phew. So this was inspired by Pillow-Mountains (on Tumblr) telling me aaaaaall about meeting Colin Donnell at the Paris Con. She's hitting 2000 followers pretty soon and this is an early present for her fantastic, multi-fandom (but mostly Olicity) blog. I posted it originally on AO3 as a gift but I thought I'd share it here too.**  
 **Enjoy :)**

* * *

Tommy sniffed cautiously at the contents of the cocktail glass. Given the lack of guinea pigs available for easy commandeering, he'd been reduced to test-driving his own drinks on a sun-drenched Wednesday afternoon.

As part-owner of a semi-successful nightclub.

Inside an old steel factory.

Alone.

God, responsibility had a way of sounding pathetic in the harsh light of day. Not that he'd had much experience in the area, since his memories of anything before four P.M. were usually of the REM sleep variety. Hard drinking and harder partying had a way of making the daylight hours dagger-like to the retinas.

Up until six months ago, at least.

Tommy turned on his heel, hunting for the picture he kept behind the bar, and raised his glass. "This one's for you, sweetheart," he said, toasting a smiling picture of Laurel Lance.

The drink went down easy, fresh liquid silver for the Verdant specials — if only he hadn't overdone it on the crushed ice.

" _And_ that's brain freeze," he said, gluing his tongue to the roof of his mouth like he was in third grade again and had overdone it on one of Raisa's famous blue grape and cherry snow cones.

His fingers were still pinching the bridge of his nose when his phone started to buzz in his back pocket. Tommy put it to his ear without looking at the display, also without unsticking his tongue from its brain freeze battle station. " _Hurroh_ ," he said.

"Tommy? Are you drinking again? Jesus, it's two-thirty in the afternoon."

Tommy's tongue unglued itself with a faint _pop_. "McKenna Hall," he said, still wincing from the head-twinge. "It's two thirty-one, actually, and I'm not drinking. Actually, I'd like to revise my previous statement, detective. I _am_ drinking, but it's cocktails. Not that I drink cocktails on my own, in the middle of the day. I own a nightclub — it's all good." He stared up at the ceiling with the phone still pressed to his ear, shaking his head at his inability to sound like he wasn't a pervert/alcoholic in front of old friends. "Did you call to check up on me?"

"Okay," McKenna said, still sounding suspicious. Not without good reason, but that was another story, for another time. "No, I'm not calling to check up on you. It's about one of your employees, actually, a…"

Papers shuffled, and he could see her looking through the crammed (but meticulously ordered) docket on her desk for a file, sitting ramrod straight in the purely terrible office chair SCPD had assigned her. Jesus, the unnameable color alone was a crime against humanity, not to mention the level of lumbar support that _had_ to be some kind of health code violation —

 _Not the point._

"Ah," McKenna said, flipping through pages. "Roy William Harper — Jr. He was brought in last night for assault while attempting to make a citizen's arrest."

Tommy shut his eyes and let his head sag forward, touching his chin to his chest. Here he was, running a business he only part-owned, a couple months into the _Big Brother_ role (thanks to Oliver going AWOL to Lian Yu), and — somehow — he'd also adopted a twenty-ish-year-old kid along the way. "What was it this time?" he said tiredly.

"A few would-be muggers outside Big Belly Burger," she said. "He almost put one of them in the hospital. The captain wanted to call the DA himself, but he ended up changing his mind."

"You mean you talked to him," Tommy guessed. "Flirted a little? Used some dirt on him? Baked some cookies?"

"He's gay — clean as a whistle — and allergic to gluten," she said. "In that order."

"So…teacher's pet, then."

McKenna laughed, but through closed lips — like she was refusing to let him score a point in their ongoing game of _Detective Hall Doesn't Actually Hate Tommy_. "I told him that I knew his mom, and he was going through a rough patch at home. I also said I'd keep him out of trouble…which is why I'm calling. I can't keep bailing him out of trouble, Merlyn."

 _Uh-oh_. The last name treatment. Cop friend was about to drop some ultimatum-level seriousness, which naturally meant that Tommy went sprinting in the other direction, right into the wall of inappropriate humor.

"You know I love it when you call me _Merlyn_ ," he said. "It makes you sound like a sexy math teacher."

McKenna snorted. "Ms. Rodriguez? Yeah, I heard what the two of you did at the ten-year reunion. You're lucky her husband isn't a cop."

Tommy felt like he'd lost a point somewhere. "Didn't know you knew about that," he muttered.

"Merlyn, I'm serious. The city's cracking down on citizen vigilantes," she said. "The captain would _love_ to make an example out of a hotshot like Harper. The DA too. Quentin Lance just cinched a promotion heading up the anti-vigilante task force, and their mantra is getting justice for what happened on the night of the Glades collapse. The city doesn't need another Hood, even if he's wearing a red Abercrombie zip-up."

Tommy didn't answer immediately. His eyes were fixed on the photo — _the_ photo. Dinah Laurel Lance, in loving memory.

She was laughing, not into the camera, but at the person taking the picture.

The same person who'd taken the photo from the frame with shaking hands and put it up at the bar, _after_. After the hospital, after the police station, after the drinking and smashed everything. After the night in front of the Queen mansion hearth, passing a bottle of vodka between himself and Oliver, forgetting that there were tears on his face and a hole in his heart where one of his best friends used to be.

He was great at being in photos, all smolder and cheekbones, which was why the discovery that he could barely handle a beginner's polaroid came as such a surprise. A laugh-yourself-to-tears discovery.

And _god_ , she'd laughed. They both had, and somehow — thank god — he'd clicked the shutter at the exact right moment, one perfect picture in a series of uncontrollable thumb cameos and blurred beige goops against the garden backdrop.

"I'm sorry," McKenna said, in a very different voice. A voice that meant they weren't playing the game anymore. "I shouldn't have mentioned it. I thought you knew."

"I saw something in the papers," Tommy answered, offhand, as though he didn't have a weekly ritual of calling Dinah every Sunday afternoon, just to keep her company while she graded student papers.

As though he wasn't keeping an eye on Quentin's visits to the doctor (not damn near enough in terms of frequency), as though they didn't run into each other at the gate of the cemetery, both carrying bouquets of white roses and stargazer lilies with bold pink hearts, and make the silent pilgrimage towards the twin graves resting quietly side by side in the shadow of a weeping angel.

"Have you heard from Oliver?" she asked.

Tommy shook his head before he realized that she was on the phone. "Uh — no," he said, deliberately not thinking about the last time they'd seen each other, or the last text message sent from an unknown number from an unknown location.

Well, technically unknown.

 _Hard to find_ was the 18th Century pirate's version of _unknown_ , and that was enough of a classification for the middle-of-nowhere that was Lian Yu.

"He's been in Europe since the funeral. Jet-skiing. Water-skiing. Lots of skiing. You know Oliver — after his dad, Laurel was just…"

"I know," McKenna said. "We all grew up together. It's like…losing an arm. You never forget what it was like, before."

Tommy looked down at his fingers, flexing them as he considered it. A phantom limb. Turning to say something over his shoulder before he remembered that Laurel wasn't behind him to hear it, thinking of a joke and reaching for his phone before he realized that the phone — _hers_ — was off, sitting in a locked desk drawer back at the mansion with a shattered screen.

He'd always been good with words, but this time, McKenna had beaten him to the perfect metaphor.

Not that he'd wanted first prize for it anyway.

"Anyway," Tommy said, sidestepping the conversational pause, a yawning gap where the silence didn't stop either of them from knowing exactly what was being said. "This was fun, and I'll talk to my idiot employee-slash-Oliver's sister's boyfriend. Don't worry about it."

"Okay," she said, and it still sounded suspicious. But in a different way. "Hey, my shift ends before opening time. How about I swing by with Chinese food? Jade Dragon?"

A grin spread slowly across Tommy's face. "But you hate me," he said. "How do I know you won't spit in the duck spring rolls?"

"Please, like you'd see that as an issue. You keep saying that's the only way you're ever getting my DNA in your mouth — which is true, by the way."

"I guess we'll never know for sure."

He knew McKenna was smiling. "I guess not," she said. "See you later, Merlyn."

"You will indeed, Detective."

They hung up at precisely the same time, and Tommy smiled at his phone for a stupid second longer before he returned it to his back pocket.

The over-iced experimental cocktail he left sitting on the bar top, and leaned back to continue his staring contest with Laurel's picture. She wasn't the only face there — after the Glades disaster, Verdant had become a local watering hole of sorts, one of the few places miraculously unharmed by the destruction, and Tommy had made an executive decision (after a few nights of pouring drinks and trading stories with the bereaved) to start a memorial corner for the dearly departed. Now there was a collage of photos from all over the neighborhood, flanking bottles of vermouth and bourbon and rows of polished glasses, all warm, smiling faces and preserved moments. Parents, children, sisters, brothers, friends.

Tommy didn't want to presume what the photos meant to other people, but to him, it was a reminder that Laurel Lance had loved the Glades. She'd dedicated a career to making it better in CNRI, and there was no way in hell that she'd have closed Verdant down when it brought jobs and benefits to an area that needed it more than ever.

Apparently the club was turning into a homing point for wannabe vigilantes too.

"This one's for you, sweetheart," he said, quieter still, and went back to work.

* * *

"Working during the daylight hours, Tommy?" Thea said, tossing her clipboard onto the bar top and sliding a coaster from the dispenser. " _Invasion of the Body Snatchers_ , or what?"

Tommy was already shaking out his newest cocktail for his _de facto_ little sister, a perfect blend of (enough) ice and classy booze, served in a frosted glass. "You know, one of these days, you're gonna have to stop being surprised that I'm taking Verdant seriously. Your brother is currently in Europe, and I'm here pouring cocktails for his little sister, free of charge, by the way."

"Hey, who took over Ollie's share of the responsibility?" Thea jabbed her pen at him with one hand and reached behind the bar for a dish of peanuts. "Rooney practically scalped you for the bourbon supply, and you didn't even realize he was doing it."

"Disregarding the fact that someone your age shouldn't even _know_ the going rate of bourbon per glass, much less the going rate in _bulk_ , you needed something to do that wasn't hooking up with your delinquent boyfriend."

"Excuse me," Thea said. " _Reformed_ delinquent."

Tommy smirked, and poured the cocktail out into a perfectly iced glass. "My mistake. Try it — I'm thinking of calling it the _Shooting Star_."

Though the crinkle in her nose made it _very_ clear what she thought of the name, Thea took a classy sip and raised her eyebrows. "Not bad. Terrible name, but that's really good."

" _That_ — is gin, violet liquor and chartreuse," Tommy said proudly, dropping a paper umbrella into the glass. "Sure to make the ladies…"

Halfway through the sentence, his caveman instincts realized that he was talking to his best friend's little sister — practically his too — and slammed into a rapid reverse.

"…drink responsibly and head home alone in a licensed taxi service," he finished, sliding the drink a little further away from her.

Thea narrowed her eyes at him. "Nice save."

"Thanks. I try."

The door banged open like it had been kicked, and Roy made his entrance with a cart full of the booze delivery. Tommy endured the obligatory kiss-and-greet from the two lovebirds by polishing a glass under the pretext that he was in need of a mirror (disregarding the perfectly functional one behind the bar).

"What're you doing after work?" Thea asked, with a goopy smile that made a muscle in Tommy's cheek twitch.

"Depends how hard my boss makes me work," Roy answered, completely ignoring Tommy (their working relationship in a nutshell). "Why? Got plans?"

"Mm…I was thinking sushi. _But_ — only if your boss lets you go. Wouldn't want to give her any trouble."

"But that's why she likes me."

Tommy had heard just about enough. "O- _kay,"_ he interrupted, bringing his arm down like a traffic barrier, the kind that stopped cars from getting run over by a passing freight train.

In this case, said freight train was Oliver, and Roy was the guy tied down to the tracks. Tommy was the one driving the Corvette and taking crappy pictures for the snuff reel.

Dark, dark stuff.

"Conversation over," he said. "Roy, I'm gonna need you to do inventory on the supply closet. We're restocking soon and I need to know everything we have. In extreme detail."

" _Tommy_ ," Thea said, well aware that it was intentional busywork.

"Don't worry, I'll drive him to get some California rolls and tuna maki if it gets too late." Tommy winked and rapped her clipboard with his knuckles. "I think I heard the office phone ring. Catch you later, kiddo."

"You know what? I don't even want to know." Thea shook her head and slipped off the bar stool. She stood on her toes to kiss Roy's cheek (how she didn't cut herself on it, he didn't know) and started off towards the upstairs office.

Silence. Bone-crunchingly awkward silence.

Roy seemed content to let it stretch on, staring matter-of-factly back at Tommy like he was the one running the show.

"Detective Hall just called," Tommy said, only belatedly realizing that there was no way of going about this conversation without sounding like he was a disappointed parent.

"She said you were arrested last night for beating up some guy outside Big Belly. What the hell? We had a deal — no more beat-downs or I tell Thea what you've been up to."

 _Goddammit._

"You never said _arrested_. You said you'd only tell Thea if I got myself thrown in jail," Roy pointed out. "They never charged me. Oops."

This was why Tommy never wanted kids. But instead of digressing into what was sure to become an embarrassing bicker session, he shifted gears. Roy Harper definitely thought he was as tough as a crowbar on the outside, but there was a marshmallow center somewhere in that kid, and Tommy was going to make sure it kept him off the vigilante track, one way or another.

So he reached for a beer mug and filled it to the perfect height of foaminess (nice way for all those years of drinking to pay off), before sliding it across the bar top to Roy.

"Listen, Ron —"

" _Roy_."

Tommy wagged his finger. "No, _Roy Harper_ is the name of my sorta-sister's boyfriend, not the adrenaline junkie with a death wish stomping the streets of Starling City, picking fights with the kind of upper body strength he doesn't have. Yeah, I've seen you with your shirt off. If a guy comes towards you with a knife, you should be running in the opposite direction like everyone else, not making citizen's arrests all over the neighborhood."

Roy pushed the beer away from him. "Look, I'm not talking about this to you, okay? You were born with a silver spoon shoved up your a—"

" _Hey_. That spoon was a family heirloom."

"You don't get what it's like, seeing everything go to hell around you and people being afraid to do anything about it." Roy's face was taut with suppressed rage, and if the guy had some beneath-the-surface anger issues, the surface was about as thick as saran wrap. "That's the world I grew up in. You're just too used to living in a mansion and a fat bank account to do anything about it."

"Look, Rory —"

" _Roy_."

"Don't care. Look at me," Tommy said, gesturing at himself. "Do you know how many women I have on my radar right now? Now why would I waste that memory space on remembering some adrenaline junkie's name when he's probably going to be in a hospital bed — best case scenario, by the way — and kicked to the curb by next Wednesday? When I could _really_ be remembering Yolanda the wine supplier and her favorite drink? Very dry gin martini with a twist. See how I have space for that because I _don't_ remember Rick Halpert?"

Roy folded his arms. "Yeah, I hear she sells great Herpes."

Hand up again. " _Hey._ It's a French wine, pronounced the French way. Like _Er-pay_ , I'll have you know."

"Sorry, I didn't get French tutoring and Bow Tie DIY," Roy snarked. "I learned how to climb a chain fence and throw a punch."

"Okay, I'm sensing that we're about to get into some uncomfortable measuring contests right now. My point is — as part owner of the nightclub where you work, I have fifty percent of a say over your next paycheck. That fifty percent might be pretty useful if Thea finds out about that car wreck in the Glades last night. You get me?"

"I'll sleep on it, boss," Roy said, managing to make _boss_ sound like an insult. He picked up a box of vodka for the supply closet, a move that seemed to target Tommy's demonstrably middling upper body strength, reinforced by the fact that his eyebrows were condescendingly raised. "While I'm _not_ doing inventory."

"Acknowledge my dominance over you!" Tommy called after him.

Roy gave him the finger without turning around.

Tommy shook his head at the bar. "Another win for Merlyn."

* * *

Tommy had his back to the doors when they nudged open. "Sorry, we're closed," he said, barely glancing at the clock. "Come back in…four hours."

"I'm not here for the drink and dance — though I'm sure it's very nice, generic music and partial hearing loss aside. Not that I'm saying your club isn't the _hip and happening_ place to be, I mean, there was a stabbing around the corner last week. Then again, there's stabbings everywhere these days —"

Somewhere in the middle of the detour-filled monologue, Tommy heaved a sigh, a big one. "Felicity, I told you I don't know where he is."

"Whoa, hey, is that any way to treat a friend? Friend-adjacent? Partially trusted confidante?" she said, climbing onto a bar stool while Diggle raised his hand in greeting.

"Tommy," he said, and they bumped fists.

"Hey, Digg — what can I get you?" Tommy tossed the rag over one shoulder with a mild flourish, enjoying one of his rare moments of proud masculinity in front of Oliver's physically imposing bodyguard.

"Just coffee, thanks. Black. I'm technically still on the clock."

Tommy gave him a look. "Your client's not even in town. Do you just stand by an empty chair and pretend Oliver's texting in it?"

"Might be easier if you told me _where_ I could find my client," Diggle said. "Then I wouldn't have to keep an eye on that empty chair."

Tommy huffed in amusement. "Nice try. Answer's still _I don't know_."

Felicity set her bright red tablet on the polished bar surface and unfolded it with a click, flexing her fingers like she was about to perform practical magic. Or — fix the office computer he'd accidentally crashed after downloading an email with questionably virus-free content.

"So, according to my previous extrapolations, there's absolutely no way Oliver's really in Ibiza, unless he's staying in a shack rated one-star on Tripadvisor. The hotel his family frequents hasn't processed any of the Queen credit cards —"

"Did you _hack_ the hotel in Ibiza?" Tommy said.

She ignored him. "— and no hits showed up on his passport. Now, based on everything we — including you — know about your best friend's off-road tendencies —"

Tommy thought it was an elegant way of summarizing Oliver's year as the Hood. "Is that what we're calling it now?"

"— he's good at staying under the radar. Now, since he's avoided using his passport — sketchy legal territory there — my guess would be someplace with heavy smuggling networks. I know he has a few Bratva connections, which points to Moscow and maybe St. Petersburg, but as you know, the Russian mob can be pretty touchy about answering questions from total strangers. Even if one of them's wearing a cute dress and her best lipstick. So unless you want the next time you see me to involve a lot more holes — I mean bullet holes, and yes, that sounded better in my head — do me a solid and tell us where to find him?"

As impressed as Tommy was with her extensive interpretation of educated guesswork, it was still a poker game, and he was better at bluffing, if not the actual _winning_ part of it. Hence, Tommy carefully schooled his face into revealing nothing. He had years of experience at _not_ being the worst liar in their friend circle, and he wasn't about to give it up for one of the biggest secrets he'd kept.

Neither of them looked particularly convinced.

 _Damn._ He was getting rusty.

Beside Felicity, Diggle cocked his head as if to reinforce the fact that the jig was up.

"Look, from what you've told me, I'm pretty sure Oliver owes you ten times over for saving his life, but he went away to get some space. He — _we_ — grew up with Laurel. You don't just get over losing someone like that, and I'm going to wait until he's ready to come back."

Tommy served up their drinks, ordered or not. "So let's just have a drink and talk, like friends, because we are. One black coffee, and one Violet Blush. New on the menu. Not the coffee — we don't serve coffee here. Coffee's for friends only."

The _Shooting Star_ had been retconned.

Felicity played with the paper umbrella in her drink, her expression nothing less than understanding. "You think we only want him back because he's the Hood."

Tommy uncapped a beer for himself and shrugged. "With the city the way it is, I don't blame you. Copycats running around everywhere — it's chaos. Oliver could bring it all back to zero in a second, I know that much."

For a second, he felt his heart lift, his spine straighten, as if the thought of Oliver picking up the bow again to save Starling was some kind of beacon, some kind of hope.

Tommy knew Oliver's state of mind too well to believe that.

"But he won't want to," he said, with finality. "He couldn't stop my father from bringing down a city, and Laurel…she's gone. Oliver never used to blame himself for anything, but he's gotten real good at it since he got back from the island."

"And you're okay with your best friend living the rest of his life in some corner of the world alone?" Diggle questioned. "His mother's about to go on trial, his sister's alone, and his family's company is about to be scrapped and sold for parts. The Oliver we know wouldn't stand for it."

"Yeah?" Tommy said. "Unfortunately, I have dibs in that area. I'm sorry about both your jobs if Stellmoor International wins the buyout, but I'm not going to tell you where to find Oliver if all it means is you bringing him back to watch his family's legacy crumble. I can't protect him with a bow and arrow or fancy kung-fu, but I _can_ protect him by making sure he's out of the crash zone when it happens."

"What makes you think all Oliver can do is watch?" Felicity said. "What makes you think he can't save Queen Consolidated from being taken over? Just for starters, by the way."

Tommy laughed without meaning to. "Oliver owns half of this place," he said, tipping the beer bottle at the dance floor. "Now his share of the work's being managed by his eighteen-year-old sister. I love Oliver, but he's not a businessman."

"Neither are you, and Verdant's reporting record profits. You're the only leisure-related business in the area keeping their head above the water," Felicity answered, without missing a beat. "You and Oliver could turn Queen Consolidated around, and that's barely even exhausting your options."

Tommy glanced at Digg, who looked unfazed. "God, you're actually serious," he said. "What, did you draw up a master plan for QC's recovery already?"

Felicity flipped her tablet around to show him the series of data tables and document bundles just waiting to be used. "My supervisor underestimates how much work I can finish before I start getting bored."

Tommy chose to maintain a diplomatic silence, opting instead to have a drink. He took a long drag of ice-cold beer, simultaneously scrolling down the painstakingly detailed recovery plan on Felicity's computer while he shot sneaky glances at her out the corner of his eye.

She seemed unaware of the scrutiny. "Hey, this is _really_ good," she said, pointing at the purple cocktail. "I think I just found my new favorite drink. But I think I have to pee to enjoy it."

Diggle made a noise under his breath, like they'd established a warning system for her verbal slip-ups.

"I _mean_ , I need the bathroom," she laughed. " _Not_ that I'd automatically have to pee while drinking this — because that would imply some pretty poor personal hygiene, am I right? Okay, I'm gonna go now. Be right back. Forget I said anything. _Obliviate_."

Tommy watched her amble off in the direction of the toilets. "Was that _Star Wars_?" he said, intentionally dense. "Wait, don't tell me — _Doctor_ something. Is that his name? _Doctor Something_?"

"Shut _u-p_ ," she called back, over the sound of a closing door.

Tommy laughed into his bottle of beer. "Sometimes I wonder if her mom pissed off a shaman while she was pregnant with Felicity, and the dude cursed her into having the worst luck with human language ever."

Diggle chuckled. "Maybe. Felicity doesn't talk about her mom too much. Sore spot."

Tommy exhaled. "Yeah, I know about those. Sure I can't get you a beer, man?"

Diggle shook his head. "Nah, with me it's Tennessee whiskey or nothing."

"Respect." Tommy went back to the plans again, trying to recall the parts of his business school education that he _hadn't_ opted out of. "Man, I really wish I hadn't skipped that accounting class."

"What happened?" Diggle said, sounding not at all surprised.

"A girl." Tommy smiled a little, and took another sip of his drink. " _The_ girl, actually. Laurel said she wanted to go to Miami — there was something about a white bikini — and I was an idiot. She was with Oliver, I was never gonna do anything, but I still went. Long story short, I missed a final and flunked out of school."

Diggle's smile mirrored his. "Happens to the best of us."

"At least Carly chose you," Tommy said, with complete and reckless honesty. "Even if it was just for a while."

They'd had the conversation before, albeit with slightly different shading each time, but Diggle had the remarkable talent of making a circle feel like a path forward, like he wasn't just banging his head against a corner and waiting for something to stop hurting.

"It wouldn't have worked out," Diggle said quietly. "Too much history. It took me and Carly a while to see it, but we got there — eventually. Oliver and Laurel would have seen it too."

Always a conversation about the _what if_.

A part of Tommy wondered if he was a little masochistic, prodding an open wound before it even had a chance to scab. As little as they had in common, what with day jobs (night ones too, apparently), life experiences and general preparedness to handle adult life, Diggle had proven surprisingly easy to talk to in the months that Oliver had been gone. The guy knew what it was like to lose someone, and sometimes Tommy thought that he'd come by Verdant on purpose, despite knowing Oliver wasn't around, just to make sure he wasn't alone in the aftermath.

As hard as it was for him not to feel a little territorial about being Oliver's best friend (maybe a little more than _little_ ) Tommy had to be grateful, because at least it'd meant that Oliver hadn't been totally alone in his crusade.

Plus, Diggle was an incredible, _understated_ level of cool.

Tommy went back to reading for a few seconds, but from what he could understand from it, Felicity Smoak had been _busy_. Like she knew Oliver would need all the support he could get. Like there hadn't been the slightest shadow of a doubt that he'd be back.

If that wasn't love, he didn't know what was.

"Hey — uh," Tommy said, trying to sound as casual as he possibly could ( _smooth as a Violet Blush_ , the tagline read) "Felicity wouldn't happen to have a _thing_ for Oliver, right? Because this…is some insane smarts she put together."

Diggle unsuccessfully hid a smile in his coffee cup. "What's it to you?" he asked.

Tommy's look in return epitomized the sarcastic _please_. "Look, Felicity's a great girl — dislike of fine beers aside — and I'm trying this thing where I _don't_ set girls up to get their hearts broken by me or my best friend. Call it amassing good karma."

"Take my word for it," Diggle answered. "Whether Felicity has a crush on Oliver or not, she'd still be trying this hard to get him home. She doesn't want anything for Oliver except for him to be a better person, and whether or not they get together has nothing to do with that."

"Bullshit," Tommy said, but without much conviction. "How'd the dummy manage that?"

Diggle seemed to appreciate his affectionate designation of Oliver as _the dummy_. "The way I see it, the universe messed with him for five full years before spitting him back out again to face the world. Maybe someone like Felicity is their way of making up for it."

Tommy didn't know which part surprised him more — the fact that it had taken him this long to catch on, or the fact that Diggle had just been watching it all happen from the side and said absolutely freaking nothing.

Suffice it to say there had been a steady march — oh, who was he kidding — an all-out Mardi Gras of women in Oliver's life, of which there had been a fair share of catastrophic endings. Tommy knew this because he'd sometimes volunteered to be the shoulder on which to cry, which had paid off in various ways he wasn't necessarily proud to admit.

An IT girl in the family company, who had minimal self-filtering mechanisms and a truly frightening proficiency in hacking (a _hobby_ , of all things) would not have been first on his list of Oliver's friends.

Note — past tense.

There were two things that really stood out about Felicity ( _she still refused to tell him her middle name_ ) Smoak.

The first thing — and the most obvious — was how incredibly intelligent she was. If Oliver's superpower was the bow and arrow, Felicity's was her brain, and Tommy had always carried a special kind of respect for women who were unashamedly smarter than he was (not a very competitive category, but still).

The second thing — and this was a _lot_ more understated — was how generous she was with the sunshine that seemed to follow her wherever she went. There were different kinds of smart in the world, the kind that made someone feel small, and the kind that made someone feel like they could do anything — whether it was to invent the world's first self-flipping pancake, crack the mystery of human flight, even save the _world_. Malcolm fell into the first category. Of that, Tommy had ample experience to back it up.

Felicity was the second, and Tommy wasn't surprised at her being part of Oliver's team. Not in the least.

Even if nothing had actually happened yet.

"Should we tell them?" he asked.

Diggle rocked so far back in his chair when he laughed that Tommy was prepared to make a grab for him. " _No_ ," he said. "Where's the fun in that?"

Before Tommy could question the pure evil of that suggestion, a door slammed somewhere in the club, and Felicity re-entered the main floor with a _phew_. "Sorry, I always get so caught up reading the graffiti on the walls," she said. "I almost peed myself trying to find out whether A.J. really did end up heart-ing K.N."

Tommy frowned, vaguely recalling the drawing in question. "You mean the one under the band poster?" he said.

"Mm-hm."

"Yeah, that's not a heart," he said briefly, and gestured to the part of the human anatomy it _actually_ meant. "Trust me, I asked."

Felicity made a face into her drink. "Oh. Good for them, but _oh_."

After a brief, but meaningful glance in Diggle's direction, Tommy rested his elbows on the bar and beckoned her a little closer. "Hey," he said. "Can you keep a secret?"

There was a gleam in Felicity's eye when she planted her arms firmly on the marble and leaned forward, so they were genuinely face to face. "You know, the last time a guy asked me that, I ended up helping him fight crime in an underground basement. That's a pretty tough act to follow."

Tommy grinned in spite of the secret he was about to tell, because there was something about her that made lying a special kind of impossible.

"Lian Yu. Oliver mentioned a guy in Hong Kong who ran flights into Pyongyang," he said, writing out what he remembered about the name and address. "I went looking for him in Hong Kong a couple years back and I talked to him myself. The guy's legit. My geography's pretty nasty, but I think the island's a pit stop on the way. It's one hell of a transfer though — you sure you want to do this?"

"Well, we've only been asking for the last two months," Diggle said sarcastically. "Why would we be serious?"

Felicity was trying to get a better look at the napkin, but at such an extreme angle that he shifted the pen from one hand to another before she broke her neck (mildly ambidextrous, one of his incredibly sparse talents). "Not to look a gift horse in the mouth or anything," she said, and added hastily, "not that you're a horse — but Lian Yu has some pretty impressive square footage and I'm pretty sure some genius decided to booby trap every square inch of that thing. Do you know where he'd be?"

" _Also_ something Oliver mentioned," Tommy said, adding a diagram to the bar napkin. "I'd check places one to three, and if that doesn't work, light a bonfire and start singing. He likes Billy Joel — you know any songs?"

"Give or take a few lines," she said. "You're messing with me right now, but I _will_ sing Billy Joel on full-blast if someone gives me a mic. Which you already know from karaoke night."

Diggle plucked the napkin from Tommy's grasp and patted Felicity's arm with the other. "C'mon. We'd better get going if we want him back in time for the Stellmoor bid."

"Thank you," she whispered, and hopped up to kiss Tommy on the cheek. "I know what this means to you."

Tommy shook his head. "When you find Oliver, give him a message from me," he said. " _Stop working on your tan and get back home, you beautiful bastard._ Can you do that?"

"Should I ask about a souvenir too?"

"Nothing made of rock. I want something shiny."

Felicity laughed. "Will do."

Tommy watched them disappear into a sunny weekday afternoon before the door creaked shut again, leaving him alone in the bar. After a moment of consideration, he reached over and drained Felicity's half-finished cocktail, shaking his head like he was getting water out of his ears.

Because he was about to do something very stupid, and unfortunately, keeping him out of _stupid_ was something Laurel Lance had done best. Usually by the scruff of his neck. "Oh, I'm gonna regret this," he said, to her smiling face above the bar, like they were having an argument of their own. "But someone needs to pull his head out of his ass."

Then, quieter still.

"He deserves a shot at being happy, right?" he whispered.

 _Goddammit, Merlyn._

The rag went flying into a shelf of glasses when he tossed it aside and he was ducking under the bar in a second, trying to get one arm in his jacket while he ran for the doors.

"Hey guys — wait up!"

Because if he was going to do something stupid, why the hell not?

* * *

 **Notes: There's definitely the potential for continuing this one, (with more Oliver Queen) but it's first and foremost a present for an incredibly awesome person. Hope you enjoyed it! :D**


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